


The Holiday Party

by Brookelyn13



Category: Teen Wolf (TV)
Genre: Aged-Up Character(s), Happy Ending, M/M, Top Derek Hale/Bottom Stiles Stilinski, Truth or Dare
Language: English
Status: Completed
Published: 2016-08-22
Updated: 2016-08-22
Packaged: 2018-08-10 10:23:24
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,140
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7841107
Author URL: https://archiveofourown.org/users/Brookelyn13/pseuds/Brookelyn13
Summary: <blockquote class="userstuff">
              <p>Stiles Stilinski will not stop until he fines out if he has a chance with the one and only Derek Hale.</p>
            </blockquote>





	The Holiday Party

College was everything Stiles had hoped for. He was passing all his classes with flying colors, he was making new friends, and he was even going to a couple of parties. Stiles hooked up with a few people, testing out the waters of his sexuality until he came to a conclusion. He was happily bisexual and surprisingly all his friends and dad took it very well. 

He wasn’t exclusive to anyone at the moment which was fine with him since he had his eyes out for a certain werewolf with striking green eyes and muscle to die for. Winter break was coming up and Stiles had a plan in mind to get said certain wolf into his bed. 

As Stiles made the long trip home he came up with multiple ways to make Derek fall in love with him. But there was one major bump in the road with his plans. He had no idea if Derek was even into dick. 

Over the years Stiles has only seen Derek involved with females and no males hence the reason he’s worried he’s barking up the wrong tree. 

But Stiles of course also has a plan to find out the true nature of Derek Hale’s sexuality. 

With all the pack coming home for the holidays, a party at Derek’s loft is inevitable. And what happens when you mix college students and alcohol (featuring some wolfsbane infused alcohol) …drunk party games including truth or dare. 

Stiles was very much looking forward to this as well as seeing all his friends. Scott and Kira went to the local community college in town, Lydia of course went to Stanford with that big brain of hers, Malia decided to stay in town and work with school not really being her thing, and Liam finishing his high school education still. Derek stayed in town to make sure things stayed safe and he also found a job at the local mechanic shop in town so it was a win-win. 

Stiles had finally reached his childhood home where he was going to drop off his bags and hug the shit out of his dad. 

But sadly he found a note on the dinner table stating that his dad was going to be working a double and he won’t be home till sometime tomorrow. Stiles frowned at the idea of not being able to see his dad till tomorrow but at least he’ll have his dad on Christmas day. 

Stiles runs upstairs to shower and change before he made his way to the loft. He settles on his favorite pair of jeans that hug his ass nicely and a grey t-shirt. He ran his hands through his hair till he was happy with it and then he was off. 

Of course he was the last to the party since he left Berkeley so late in the day. But when he rolled the heavy door open he was ambushed with hugs and drinks. 

Scott nearly crushed him forgetting how fragile Stiles really was and cracking his back a bit. But he was quickly forgiven when he flashed his puppy smile. Kira and Lydia came over next with big grins plastered on their faces. Liam gave him a smile from across the room where he was sitting on the couch snuggled up against Hayden. 

Stiles’ eyes roamed over the room in search of Derek when he finally spotted the wolf coming out of the kitchen with a red solo cup in his hand. 

Derek finally sees the Stiles has arrived and walks over to him. To Stiles’ surprise Derek slings his arms around Stiles in a firm hug. “It’s good to see you Stiles.” Derek says in his ear, almost in a whisper. “You too Derek.” He responds. 

Derek releases Stiles as Scott pulls him to the kitchen to get a drink. 

*********** 

After about an hour of storytelling about college and town gossip, someone (maybe Scott) said they should all play a game of truth or dare. Stiles smiled to himself thinking how easy the start of his plan was. 

Everyone, including Derek, was game to play since everyone was happy and floaty from the booze. 

Things started out innocent with simple questions and easy dares. Until more alcohol was brought into the mix, then things started to get sexual. 

“I dare you to kiss Lydia. AND it has to last at least 5 seconds.” Scott tells Kira as she starts to blush. Lydia just rolls her eyes and beckons Kira over with her pointer finger. Kira crawls over and just shrugs and presses her lips against Lydia’s. 

Woos and whistles erupt throughout the room until they pull away. Kira crawls her way back to Scott’s side and playfully hits his shoulder. 

“Alright alright everyone settle down, it’s Derek’s turn.” Stiles says with a grin on his face. Here goes nothing. 

“Derek, truth or dare?” Stiles says. “Truth.” Derek responds like he has for all the other times he was asked. 

“Do you like men?” Stiles asks. 

The room falls silent by the sudden question and all eyes fall on Derek waiting for his response. Derek takes a swig of his drink then answers, “No.” 

Stiles nods his head then takes a long sip from his drink. Liam continues on with the game after a few moments of awkward silence. 

Everyone carries on with the night as Stiles broods on the couch just sinking into the background. Ubers were called since no one was in the right state to drive and people slowly started to head home. Stiles gave Scott a goodbye hug before he carried a very “happy” Kira down to the waiting car. 

Stiles stays back to help Derek clean the loft a bit before he leaves. 

They silently begin to throw plastic cups into trash bags and pack up the extra food. The loft starts to look presentable once again. Stiles ties up the last trash bag and throws it in the corner with the rest. He shuffles his way into the kitchen where it looks like Derek has finished his duties as well. 

“Thank you for staying behind and helping. I really appreciate it.” Derek states. 

Stiles shrugs his shoulders then responds, “It’s no problem, Didn’t really feel like going to an empty house anyway.” 

Silence fills the air once again as Stiles just looks at his feet waiting for Derek to say something. 

Stiles hears Derek’s footsteps as he approaches him. Stiles eyes remain on the ground as Derek just stands in front of the younger man. 

“Is something wrong, Stiles?” Derek asks. 

Stiles lifts his head to answer the man, “Nope, just dandy.” 

“You sure, you’ve been in a mood ever since truth or dare.” Derek asks. Stiles shrugs his shoulders again, not sure how to respond. 

“This doesn’t have anything to do with that question you asked, does it?” Derek asks. 

Stiles lets out a sigh and finally responds. “It’s nothing Derek, it was just a stupid question. You don’t like men, it’s fine.” 

“Your right, I don’t like men.” Derek says. Stiles divert his eyes to floor again, but then he feels a hand lifting his chin up to stare at the older man. 

“But I do like you Stiles, I like you a lot.” Stiles eyes widen at the sudden declaration. Derek chuckles at his response and moves to press his lips against Stiles’. 

Stiles finally got with the program and started to kiss Derek back. He brought one hand to wrap around Derek’s waist to pull him flush against his body and the other hand to tangle in his soft black hair. Derek does the same and starts to grind his growing hard on into Stiles’. 

They make out furiously for a few more minutes until they pull apart to suck in gulps of air. They pant for a few moments till Stiles speaks up, “Wanna continue this in your bed?” 

Derek can’t even respond with words. He grabs one of Stiles’ hands and rushes them both up the spiral staircase to his bedroom. 

Stiles doesn’t have time to look around the room. Derek pushes the younger man onto the bed. Stiles tugs at the bottom of his shirt to lift it off. Once off he tugs the zipper of his pant down and shimmies out of those as well. 

Once Stiles is only left in his boxers, Derek begins to take off his clothes in a very sexy strip tease. He slowly lifts his Henley over his head, his chest muscles flexing as he does so. Next he kicks off his boots and slowly unbuttons and unzips his tight jeans. 

Stiles mouth just hangs open as he watches more and more skin revealed to him. Derek than slowly crawls over Stiles body until they he reaches his neck where he starts to pepper kisses and licks. 

Stiles moans like a porn star. Derek just keeps at it with leaving multiple hickies on the man’s neck and color bone. 

“Derek please I need more.” Stiles moans. Derek gets the message and starts to slide his body and mouth down the rest of Stiles’ body. Derek plays with his nipples for a bit, enjoying the reaction Stiles got at the lick at the small pebbles. 

Derek continues his way down Stiles’ chest and completely bypassing his throbbing erection. Derek tugs the boy’s boxers down with his teeth, releasing the boy’s member. 

Stiles whines at the lack of attention towards his dick. He lifts his head when he feels Derek shift away from him, curious as to why. He sees Derek leaning over to the nightstand next to his bed. Derek then returns with a bottle of lube and a condom. 

Stiles heart pounds with excitement and a little bit of nervousness as Derek pulls down his own brief to reveal a very hard and very big erection. Of course Stiles has had sex before, but none as big as Derek. 

Derek picks up on Stiles’ nervousness, “If your too nervous Stiles we can just make out some more if you’re not ready for sex.” 

Stiles shakes his head and quickly responses, “No no no I definitely want to have sex with you, it’s just, you’re so big I just got a little nervous.” 

Derek smirks at the boy and gently kisses him. 

“Don’t worry, I’ll go gentle.” Derek says. Stiles nods his head and leans back against the pillows as Derek lubes up a few fingers. 

He trails a finger up the cleft of Stiles’ ass until he reaches the puckered hole. Stiles lets out a moan as Derek slides a finger into him. Derek moves the finger in and out, slowly open Stiles. 

“Derek, more I can take more, please.” Stiles begs. Derek then inserts another finger in and scissors Stiles’ hole. Then another finger slide in with the first two. 

“Are you ready Stiles?” Derek asks. Stiles can only nod his head, speechless with arousal. 

Derek slides the condom on his thick cock and lubes it up. He then lines his cock up to Stiles’ hole and slowly pushes in. Stiles lets out a loud moan at the intrusion that is Derek’s huge dick. 

Derek eventually slides all the way in and waits a few moments for Stiles to adjust. 

“Derek…. move!” Stiles breathes out. 

Derek nods his head and slowly pulls out then slams back in. Stiles moans as Derek nailed his prostate over and over again as he just pounded into his ass. 

Stiles hooked his ankles around Derek’s lower back and wrapped his arms around his neck to pull him into a furious kiss. 

Derek braced his knees on Stiles’ sides and pounds faster and faster feeling his orgasm approaching. 

“God Stiles you feel so good around me. Like you were made for me.” Derek pants out. 

“Yes Derek fuck I love your cock in me!” Stiles moans as he starts to bite into Derek’s shoulder feeling his orgasm approaching. 

“Derek… I’m close.” Stiles says. Derek then grabs Stiles’ cock and pumps in time with his thrust. 

Stiles couldn’t hold it anymore and screamed Derek’s name as he came in-between their stomachs. 

Derek came seconds later as Stiles squeezed around him like a vice. 

They pant and come down from their orgasms, gently kissing and touching each other. 

Derek slowly pulls out of Stiles and takes off and ties off the condom. He then goes to his bathroom to clean up and returns with a wet washcloth to clean the cum off of Stiles’ stomach. Stiles just lays their as Derek cleans him, grateful for the man not making him do much. 

When Derek comes back, Stiles wraps himself around the man and slowly begins to fall asleep. He kisses Derek once more and the lips and whispers, “Best holiday party ever.” 

Derek chuckle and then responds, “Agreed.” 


End file.
